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离子液体在结构化二十二碳六烯酸溶血磷脂的酶促合成中的应用。

Use of Ionic Liquids in the Enzymatic Synthesis of Structured Docosahexaenoic Acid Lyso-Phospholipids.

作者信息

Garcia-Quinto Ernestina, Guisan Jose M, Fernandez-Lorente Gloria

机构信息

Laboratory of Microbiology and Food Biocatalysis, Institute of Food Science Research (CIAL, CSIC-UAM), Nicolás Cabrera, 9, UAM Campus, Cantoblanco, 28049 Madrid, Spain.

Department of Biocatalysis, Institute of Catalysis and Petrochemistry (ICP, CSIC), Marie Curie, 2, UAM Campus, Cantoblanco, 28049 Madrid, Spain.

出版信息

Molecules. 2025 Feb 6;30(3):728. doi: 10.3390/molecules30030728.

DOI:10.3390/molecules30030728
PMID:39942830
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11819881/
Abstract

Recent studies have shown that DHA supplementation in the form of phospholipids effectively increases DHA levels in the brain, including DHA lysophospholipids. This research explores a method to produce DHA lysophosphatidylcholine (DHA-LPC) using lipases and phospholipases immobilized on Immobeads-C18 with maximal enzyme loading. The esterification of glycerophosphatidylcholine (GPC) and DHA was studied with ionic liquids as alternatives to traditional solvents, with 1-methyl-3-octylimidazolium tetrafluoroborate (MOIM-BF) providing the highest yield due to its ability to increase the solubility of GPC. The reaction parameters were modified to establish a molar ratio of GPC to DHA of 1/10. A maximum DHA-LPC yield of 80% was achieved in 48 h, with a formation rate of 20.06 (mg/mL.h) × g. The Quara LowP biocatalyst (QlowP-C18) maintained 100% activity during the first three cycles and produced 788 mg of DHA lysophospholipid. The use of 50% MOIM-BF improved the stability of the biocatalyst, and NMR confirmed that the product was the sn1-DHA-LPC isomer.

摘要

最近的研究表明,以磷脂形式补充DHA可有效提高大脑中的DHA水平,包括DHA溶血磷脂。本研究探索了一种使用固定在Immobeads-C18上的脂肪酶和磷脂酶以最大酶负载量生产DHA溶血磷脂酰胆碱(DHA-LPC)的方法。研究了甘油磷脂酰胆碱(GPC)和DHA的酯化反应,使用离子液体替代传统溶剂,其中1-甲基-3-辛基咪唑四氟硼酸盐(MOIM-BF)由于能够提高GPC的溶解度而提供了最高的产率。修改反应参数以建立GPC与DHA的摩尔比为1/10。在48小时内实现了80%的最大DHA-LPC产率,生成速率为20.06(mg/mL·h)×g。Quara LowP生物催化剂(QlowP-C18)在前三个循环中保持100%的活性,并产生了788mg的DHA溶血磷脂。使用50%的MOIM-BF提高了生物催化剂的稳定性,核磁共振证实产物为sn1-DHA-LPC异构体。

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本文引用的文献

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Green biosynthesis of DHA-phospholipids in tailor-made supersaturated DHA aqueous solution and catalytic mechanism study.在定制的过饱和 DHA 水溶液中进行 DHA 磷脂的绿色生物合成及催化机制研究。
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Enzymatic synthesis of mono- and disubstituted phospholipids by direct condensation of oleic acid and glycerophosphocholine with immobilized lipases and phospholipase.
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Insights into the effect of imidazolium-based ionic liquids on chemical structure and hydrolytic activity of microbial lipase.咪唑基离子液体对微生物脂肪酶化学结构和水解活性影响的研究进展。
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DHA Esterified to Phosphatidylserine or Phosphatidylcholine is More Efficient at Targeting the Brain than DHA Esterified to Triacylglycerol.与酯化到三酰基甘油的 DHA 相比,酯化到磷脂酰丝氨酸或磷脂酰胆碱的 DHA 更能靶向大脑。
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